Stockbridge Vacation Packages 2026 from $654

Stockbridge flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

$654

per person

Oct 13 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) to Albany (ALB)

This hotel features a 24-hour gym and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Spacious Home in Troy

Save 100% on your flight

$827

per person

Oct 13 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) to Albany (ALB)

Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.

South Shire

$972

per person

Oct 16 - Oct 20

found 23 hours ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, express check-in, and express check-out are also on offer.

Four Points by Sheraton Albany

$663

per person

Oct 13 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) to Albany (ALB)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Hyatt Place Albany/Downtown

Downtown Albany

$870

per person

Oct 13 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) to Albany (ALB)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Top Stockbridge hotels deals

The Red Lion Inn

30 Main Street Stockbridge MA

Free Cancellation

Reserve now, pay when you stay

$228 nightly

$254 total

Aug 23 - Aug 24

Total with taxes and fees

This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

26 Glendale Road, RR 183 Stockbridge MA

$358 nightly

$399 total

Aug 24 - Aug 25

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.

The Inn at Stockbridge

30 East Street Stockbridge MA

$427 nightly

$477 total

Aug 12 - Aug 13

Total with taxes and fees

This bed & breakfast features a 24-hour gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A garden, a lobby fireplace, and a communal living room are also on offer.

Pool

Breakfast included

Historic Stockbridge Villa on 25 acres

Stockbridge MA

Get rates

This vacation home features an outdoor pool and a sauna. Families will appreciate the playground and barbecue grills. A garden and laundry facilities are also provided.

Pool

Kitchen

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$143 total

Aug 31 - Sep 1

Total with taxes and fees

This aparthotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

The Yankee Inn

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$175 nightly

$195 total

Aug 10 - Aug 11

Total with taxes and fees

This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Stockbridge attractions

Norman Rockwell Museum

9.4/10 (347 reviews)

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

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Frequently asked questions

How much are vacation packages to Stockbridge?

Epic adventures await in Stockbridge, with Travelocity vacation packages from as low as $654. Providing both flights and hotels, these terrific deals are a simple way to visit more of our wonderful planet.

How long should my Stockbridge vacation be?

Many visitors stay roughly 2 nights in Stockbridge. But what works for them mightn't work for you. Whether you opt to stay for a few days or a few weeks, you'll enjoy discovering all the wonderful things that this place has to offer.

Where can I get the best vacation package deals for Stockbridge?

There are awesome Stockbridge package deals to be snapped up with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties across the globe? Keep that in mind the next time you're ready to cross another place off your travel bucket list.

Why should I book my Stockbridge vacation bundle with Travelocity?

Because we believe in creating unforgettable travel experiences. From hotels and flights to car rentals and activities, we put everything at your fingertips. Our customer support is on hand 24/7 to make sure you're never alone. We also offer a Price Match Guarantee, so you can book your trip knowing you've scored the best deal around. If you find a lower price, we'll match it!

Can I save on my Stockbridge car rental if I book it with my hotel or flight?

Combining your flight, hotel and car into a Stockbridge vacation package is the best way to score better prices. Plus, having your own wheels gives you total freedom to get to all those big sights you'd like to see. Sitting 110 mi away from Stockbridge, Times Square is one attraction that should be on your can't-miss list. Fasten your seat belt and make a day trip of it.

Which airport is best for Stockbridge?

Bradley Intl. Airport (BDL) is popular. It's situated approximately 40 mi southeast of Stockbridge. Other options worth considering are Albany Intl. Airport (ALB) (40 mi away from central Stockbridge) and Hartford, CT (HFD-Hartford - Brainard) (50 mi away from central Stockbridge).

What is there to do in Stockbridge?

There is a certain magic as you wander through the streets of Stockbridge. National Shrine of the Divine Mercy and Norman Rockwell Museum are just a couple of attractions that make this city such a sought-after destination, so put them at the top of your to-do list.

Where should I stay when visiting Stockbridge?

The The Red Lion Inn is recommended by many travelers. Book now before it's too late.